Sodium borohydride → 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazol-6-ol

HRID 1803265Notes

Reaction equation

HRID 1803265 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[S:15][C:16]4[CH2:22][C:21](=[O:23])[CH2:20][CH:19]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:17]=4[N:18]=3)=[CH:9][C:8]=2[O:31][CH3:32])[CH:6]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[S:15][C:16]4[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:17]=4[N:18]=3)=[CH:9][C:8]=2[O:31][CH3:32])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 581100012-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one

Product 1

HCID 581099972-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzo[d]thiazol-6-olYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-4-(4-fluorophenyl)-4,5-dihydrobenzo[d]thiazol-6(7H)-one (5.0 mg, 0.011 mmol, from example 75), sodium borohydride (1.2 mg, 0.032 mmol), and methanol (0.050 mL) were stirred at rt for 1 h. The crude reaction was quenched with brine solution and extracted with EtOAc. The organic layer was concentrated in vacuo to afford 4.0 mg (76% yield) of the titled compound as a brown oil. LC-MS (M+H)+ 471.2. 1H NMR (400 MHz, methanol-d4) δ ppm 7.82 (d, J=2.01 Hz, 1 H) 7.63 (d, J=1.51 Hz, 1H) 7.33 (s, 1 H) 7.17-7.24 (m, 3 H) 7.13 (d, J=8.56 Hz, 1 H) 7.02 (t, J=8.81 Hz, 2 H) 6.64 (dd, J=8.56, 2.27 Hz, 1 H) 4.00-4.23 (m, 3 H) 3.33 (s, 3 H) 3.04 (dd, J=15.23, 5.41 Hz, 1 H) 2.70 (ddd, J=15.30, 9.76, 3.15 Hz, 1 H) 2.29-2.42 (m, 1 H).

Workup

  1. customThe crude reaction
  2. customwas quenched with brine solution
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-cc75fe02152b4b99ae738d0a5c7d19f1
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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